When Will the Stock Market Crash Again?

Ben Carlson and Duncan Hill answer listener questions on whether fewer recessions mean fewer stock market crashes, planning for a parent's retirement housing gap, real estate versus levered stocks, discussing finances with aging parents, and sustainable withdrawal rates under inflation. Ben argues that stock market crashes will still occur despite fewer recessions, that real estate has structural advantages and lower volatility, and that retirement withdrawals benefit from balanced portfolios and cash buffers. - Fewer recessions have not eliminated bear markets; crashes remain a recurring risk. - A short-term bond/CD ladder can cover near-term retirement spending gaps while longer-dated target-date funds grow. - Real estate offers leverage, tax benefits, rental income, and lower price volatility compared with stocks. - Retirement withdrawal portfolios may be safer with 60/40 to 70/30 allocations and cash buffers rather than all stocks. - Conversations with aging parents about finances are difficult but important, with fraud and cognitive decline risks rising. - Inflation affects sustainable withdrawal rates, but historical impact is less dramatic than often assumed.